A Frightful Night
by Kakashifan727
Summary: Friendship!ReaderxJack Skellington COMPLETE You become lost one Halloween, stranded in the woods near town, thanks to the antics of some mean big kids. You thankfully meet a nice, tall costumed gentleman who offers to walk you home safely. You learn about what it means to be strong, and how being afraid isn't necessarily a bad thing.
1. Chapter 1

You had been so excited to go out tonight. You enjoyed Halloween; and this was your first outing with the so called 'big kids'. They had been nice enough to allow you to tag along this year, and you had been ecstatic at the prospect of being seen as more than a 'little baby'.

It was fine at first, all of you going up to houses and getting the usual one piece of candy; though you noticed some of the older kids grabbed more if they could get away with it. Things continued like this for a while, you happily strolling along behind them in your little costume with your trick or treat pail, going along the neighborhood house by house until there were no houses left.

Then one of them had made a suggestion to go into the woods as a sort of shortcut to reach the other neighborhoods around town. They said it was for better candy, and who were you to say no to that? Not like you could protest, small, tiny thing that you were. You wanted them to see you as a big kid, not a little child, and so you said nothing despite the trepidation making your heart beat faster in your chest. Though you had felt a tiny shiver go down your spine as some of the kids stared at you, their gazes somewhat menacing in the dark of night. What was there to be afraid of, you told yourself? You were five years old; certainly big enough to do something like this by yourself. Besides, it's not like they would leave you all alone in the woods as they ran off to find candy, would they?

Oh, how naive you were!

You tried to run as fast as you could after them, your stubby little legs not as nearly well equipped to traverse the uneven terrain. The small pumpkin shaped container that held your candy rattled continuously as it kept bouncing and slapping against your side, candy sometimes spilling out and forcing you to stop running to pick it up every so often, fear building in your gut as you saw their forms get farther and farther away. They didn't really seem to notice you, and you thought you heard some of them laugh in the distance, but you couldn't be too sure.

"Wait for me!"

Your weak, tiny voice cried out, a last ditch attempt to get them to notice you. Not a one of them turns back, making you wonder if you didn't shout loud enough. You try shouting once more, hearing your voice crack somewhat due to fear as it is swallowed by the darkness. You were all alone then, their figures nowhere to be found in the dark expanse of trees. They had left you, running off somewhere in their rush to acquire more candy, and possibly trick more people while they were at it, and you were now on your own.

It was scary for you to be here, the wind's whistling sounding almost like howls to your young ears and the trees' large branches looking like claws that would grab you up in an instant and snatch you away to who knows where. You felt your heart catch in your throat, effectively stopping any further attempts to cry out that you tried. You shivered as you felt the cold wind bite your skin, unsure of what to do or where to go as your eyes darted to and fro. No, you weren't going to cry, you tried telling yourself. You were a big kid now; Big kids didn't cry!

Still, despite your best efforts, you felt your eyes start to burn as your vision became blurry, tears trailing down the side of your face as you let out a tiny sob. That small sob turned into one of many, your tiny body slumping against a tree trunk as you huddled your arms around yourself. What were you going to do?

The lanky skeleton carefully extricated himself from the tree hollow, being cautious not to bump his head on any of the taller branches. If only the trees in the human world were able to grow as big as they did back in Halloween Town, he mused as he dusted off his suit. Though, 'Halloween Town' was still more of an idea than an actuality; the place mostly empty and abandoned aside from himself, which was quite a sobering thought for the tall skeleton. Trying to build a town wasn't easy; there were a lot of small things needed to get it going. Sometimes the trip between the two realms was more than he had bargained for. But, it was worth it, he thought, for him to be able to go out and terrify the humans. Here, he felt, he could truly practice his craft. And possibly distance the odd, creeping loneliness in the depths of his heart.

Scanning the forest, not entirely sure where he had ended up this time, the skeleton began walking at a somewhat leisurely pace. He hoped to find some unaware humans with which to practice his spooking technique; Jack not entirely confident in his ability to scare people. Ever since he had 'awoken' so to speak, he just understood that was his calling; what he had been brought into the world to do. And so he had tried to practice his craft as much as he was able.

The sound of crying made him pay more attention to his surroundings, the noise slightly out of place in these dark woods. It didn't sound like the hysterical crying of someone who had just been scared out of their wits; the skeleton would know that sound anywhere. Or at least, he hoped he would, seeing as he was getting better at scaring humans every time he came into the human world.

This...wasn't that.

The pitch and tone of the sobs were easy for him to follow, even in this dense forest, curiosity making him want to seek it out just for the heck of it. The tall tees and creeping foliage were of little obstacle to Jack, his long legs easily able to stride over the inconveniences as he crept along. Soon enough, he came upon the source of the sound; a small, huddled child, tears streaming down their red face.

He only looked at the tiny, shaking figure on the ground from a distance, not wanting them to spot him and run off, it's pitiful cries making something inside him ache. They were only a child, after all; And an extremely small one at that, Jack reasoned, going by their size. Then again, he was quite tall himself, well over the size of a normal human male, so maybe he could have been mistaken. It had been a while since he had went out into the human world to scare someone, after all.

The thing was truly terrified, going by the hiccuping sobs it made; and not terrified the way that he usually preferred his scare victims. There was fear, and then there was _fear_ , and this seemed to him like a case of the latter. He didn't like it; what kind of...jerk...would leave a small child out here in the woods all alone? This certainly seemed like a place not suited for a small child. The skeleton wasn't sure of what he could do to help, seeing as he was an outsider who rarely intervened in human affairs—aside from scaring the daylights out of unwitting humans—but he wasn't just going to stand here and do nothing!

But, Jack was concerned about scaring them, a slight smile coming to his stitched lips as he understood the irony of the situation. He wasn't exactly drop dead terrifying, only when he wanted to be, but a small, confused and frightened out of their wits child might think otherwise. He didn't want to scare them and cause them to run off deeper into the woods; they could get hurt. Then again, he reminded himself, it _was_ Halloween, after all. The child might just see him as someone wearing a costume, albeit much more detailed than normal. His mind firmly made up, Jack made sure to move towards them as loudly as possible to announce his presence.

You weren't too sure how long you just stayed there, sobbing. It felt like ages, the cold wind brushing against your cheeks, your shoes buried deep in the cold, damp soil where you sat for what seemed an eternity. You didn't want to go anywhere else, too afraid that you'd get lost further and no one would be able to find you. So, the best thing your tiny mind decided was to stay here, in case maybe one of the bigger kids came looking for you. You hoped they would, anyway.

Hearing a noise to your side, you nearly let out another sob as you saw _something_ emerge out of the brush _._ It was hard for you to make out what it was, seeing as your vision was blurred from the tears streaming down your face. It was a tall, thin person, and you could watch in surprise and fear as they crouched down to your level. It took you a moment to realize it was an adult—or maybe a teenager—wearing a costume; the lack of light making it more difficult to make out their features. You just waited as they stared at you with a concerned look in their eyes.

"What's this? Did you get lost? You poor thing; it's scary out here at night for a child your age! Where are you parents? Are you with anyone?"

They didn't scare you, even though you were told numerous times to not talk to strangers. Maybe it was because of the odd looking smile on their face, the calm tone of their deep and melodious voice or how they gestured to you, but you felt an odd sense of peace despite the fear making you nervous. Maybe it would be ok to let them help you; it was certainly better than sitting here in the cold and crying! You just do your best to give them piecemeal details of what happened, in between small sobs, your mind too flustered to remember everything clearly. They listened patiently, coaxing it out of you gently with questions and suggestions.

"...I-i d-don't...I-I-I—"

You tried to say, before you burst out yet again into tears. You couldn't help it; you were just so scared and flustered. The person didn't seem to mind at all, even going so far as try and keep you calm,

their oddly soothing voice assuring you that everything was going to be ok. You felt something silky and soft start to wipe your cheeks then, your eyes blearily opening to see the strange person holding a handkerchief, long, gangly arms carefully mopping up your tears and slobber. That made you feel a little bit better, and you try to continue through racking sobs. They are nice enough to try and put a hand on your shoulder, their voice calm as they comfort you.

"Don't cry; there, there now. Just try and tell me what happened!"

Their voice is nice and gentle, soothing, and almost reminding you of something. It helps calm you, and you try to explain once again from the beginning. You even go so far as to give the person some descriptors of the big kids you had been trick or treating with. If they were an adult, and they seemed trustworthy to you, maybe they could help reunite you with the others. Though most of you just wanted to go home by now; you were tired, and cold and maybe even a little peckish. The tall person only attempts to look you in the eyes once more, and you follow suit, curiosity making you anxious.

"That's horrible! You must be terrified! While it is Halloween, and I do _love_ a good scare, this is pushing things!"

You hear them say, their voice rising in volume and deepening as they spoke the last sentence. They must be angry about it, you guess. You weren't really sure and didn't care; you just wanted to go home! You watch as their expression shifts suddenly, the odd cloth covering their eyes widening in surprise as they smiled at you.

"Ah, with all that was going on, I nearly forgot to introduce myself! You may call me Jack, little one. Would you give me your name?"

You nod, giving your own name as you were taught to do. Jack just smiled again, even going so far as to pat your head a couple times.

"So, [Name], is it? How nice to meet you! Maybe we should try and get you home, yes? Come with me; I'll keep you safe."

You let him grab your hand then, the feel of it odd to you as it wrapped around your much smaller hand. It was hard, and slightly chilly, and textured differently from any other hand you had held before. Despite this, it wasn't uncomfortable, just different. You just didn't feel scared around Jack; quite the opposite really. You felt safe, calm even. He carefully began to walk, his long legs dwarfing your stubby limbs as you both moved through the woods. He seemed to be conscious of this however, being careful not to walk too fast for you. You just followed him through the woods as best you were able, not wanting to be left behind. After a while, Jack began to speak, you listening intently.

"Are you ok? Let me know if you're tired, alright? Do you need me to carry you?"

"No, I can walk...T-thank you, mister."

You mutter, hanging your head down slightly, sort of shy and nervous. You just feel Jack's suddenly tug on your arm stop then, the tall costumed adult turning your way once again. You couldn't really tell what expression he was making, but your stomach still was slightly unsettled as you watched him crouch down towards you again.

"What's wrong? Are you sure you're ok?"

"..."

You can't really answer him, since you weren't too sure yourself. You try to say something though, not wanting to be rude seeing as he asked you a question.

"I'm ok…"

"You don't sound ok. Are you still scared?"

"...N-no."

You lie, and he can obviously sense it, going by the frown on his spherical face. He sighs, shaking his head as he regards you.

" _Everyone_ gets scared. Just because you're afraid doesn't mean you're not brave or strong."

"E-everyone? Even adults? The big kids called me a crybaby. I don't wanna be a crybaby anymore. I want to be big and strong! If I can't be scared, I'm strong, right?""

He heard the child mutter, the semblance of an idea coming to Jack suddenly. He let out a small chuckle then; children really were quite precious. They saw things differently than how cynical adults or teenagers did; more simply, more pure hearted. Which was probably why he often targeted older humans on Halloween; to show them that they could still be scared out of their wits. That, and it was quite a challenge for Jack; he also saw it as a way to improve his skills.

It was one of the few things he understood to be his purpose, something that gave him a sense to keep on going, despite the uncertainty for the future he held. He quite enjoyed watching fully grown men be reduced to sobs and shrieks after one of his tricks was successful. It was much more satisfying to him than scaring a small child. He rather liked children. Jack only offered the small child a sincere smile as one of his long arms reached out to pat them on their head.

"Of course! Fear isn't a bad thing. Not at all! It's very good!"

"It is?"

He stopped speaking then, his bony hand cupping his chin in thought. Explaining the nuances of fear to a small child was not exactly easy. Maybe there was some way to show them... _That's it!_ A mischievous smirk lit up his face, sockets narrowing as he thought up a plan. Maybe there was a way to give them payback for what they had done to the small child, and he could get some good scares in as well. And, the child could learn a lesson about how fear was a good thing, something positive, not negative. Yes, that was it.

"Being afraid isn't a bad thing. Maybe I can help teach you why; after we find those bullies!"


	2. Chapter 2

He can hear them before he sees them, their voices echoing loudly in the still autumn night. There were at least three of them, going by the different tones and pitches of their squeaky voices. They were laughing as they walked through the dimly lit neighborhood, babbling and chatting happily with one another. Jack noticed he could hear snippets of their conversation as they came closer to the group.

"—wet themselves—"

"—brilliant idea to ditch 'em!"

"—Stupid kid, cramping our style—"

The group erupted into raucous laughter then, and he felt the warm, tiny hand gripped around his stiffen. The child looked like they were going to cry again, eyes watering and lip trembling. He unconsciously lifted his free hand to his chest then, the child's despondent look making a small frown appear on his face. Jack didn't like this situation at all. Those kids were being quite cruel, he thought, and to a small child, no less! That was something he personally couldn't ignore. Maybe a good spook or two would get them to change their nasty attitudes. And, he hoped, put a smile on the young child's face.

With that idea in mind, the tall skeleton stopped walking, being careful to maneuver the small human so they wouldn't bump into him. They just give him a curious look, their huge eyes staring at his empty sockets. He gently put a hand on their shoulder then, once again bending down so he was more level with them.

"Do you want to see something interesting? I think you'll enjoy it."

The child only titled their head quizzically at him, bright eyes blinking rapidly as they took in the expression on his skull. Jack began to step away from them then, standing up to his full height.

"Watch carefully. I'll show you some real tricks!"

An odd lightheartedness came over him then, knowing he was going to give those bullies a well deserved scare. Nothing too bad; just enough to let them know exactly who they were dealing with. So they wouldn't be so cruel to this poor child ever again. At least he hoped it would end that way; humans, he remembered, were sometimes worse than the meanest monsters. After giving the small child a hearty grin, Jack carefully slipped into the shadows, concealing his presence. They just watch him, eyes as big as saucers due to awe, before he easily moves towards the group of older kids. They were completely oblivious to his presence, busy chatting and laughing amongst themselves.

Perfect. They would never see it coming.

He only bided his time, waiting until the group came closer before jumping out of the shrubbery with a loud cry, stretching his face into the most terrifying shape he could think of, teeth flashing with a menacing glint, his large body towering over them. They let out several screams of terror, some of the kids even dropping their trick or treat pails in their panic. Jack wasn't done there however; slipping once again into the darkness after the fleeing children, hoping to catch them off guard. He easily moves ahead of them, using his shadow as an extension of himself, skeletal hands extended as if he was going to grab them, before letting out a long wail. Ear piercing shrieks of terror greet him then, several of the children just toppling over in their fright, breaking down right then and there, sobbing as tears stream down their face. Good. Maybe now they would understand a fraction of the terror the little one had felt because of their actions, Jack hoped.

The skeleton smiles at his handiwork, stepping out into the moonlight now, hands on his hips as he looks over at the frightened bullies. They were whimpering and in fetal positions; every time he moved they let out small shrieks of fright. Good. He then regards the small human once more. They were looking at him with a mixture of surprise and wonder, small mouth open in a tiny 'O'. It gave Jack mixed feelings; part of him enjoyed their admiration, proof that his scaring skills were getting better. And yet part of him was sad, knowing that their time was soon to be cut short. They truly were interesting; brave, for one. Most people, even adults, would be scared out of their minds after the display they had just witnessed. Yet this one, this small child, was smiling and happy; though he did detect a small trace amount of fear there. He just knew that the innocent look the child gave him warmed his bones; proof to Jack that he had done the right thing. Or at least he felt it was right...

"I think I'll take this…"

You watch as the tall adult reaches out to grab the fallen pail of candy. He looks at it with a an odd smirk, the candy inside jingling as it sloshed around in the bucket, and you feel yourself smiling along with him. He really was interesting, the way he scared those kids like that, and yet he was so calm and considerate with you. You hadn't even felt scared when you saw him trick those kids; whereas usually you'd be terrified of such antics.

Maybe it was because of the short amount of time you'd spent together, but Jack wasn't really 'scary' in your mind. He was cool, even; and part of you wanted to be as terrifying as he was. Well, maybe not terrifying—you weren't exactly sure what it was you felt. But you did know you wanted to become more brave and able to fight back against bullies like the ones who tormented you.

You hear the concerned voices of more adults coming your way, probably attracted by the screams and cries of fright elicited by the older children. You also notice Jack move away from you, his figure blending easily enough into the darkness. Part of your chest began to ache at the realization that he was leaving; not exactly fancying being left alone with the bigger kids that were now sobbing wrecks on the ground in the dark.

"Aw, you're leaving...?"

"I'm sorry, [Name], but I have things to do. It seems like some adults are coming this way too. You should be quite alright without my help now. I did have quite an interesting time with you, though!"

You felt his oddly textured hand run through your scalp then, petting it fondly as he bent down to your level once more. Despite the voice in your head telling you to be strong, you felt tears well up once again at the corners of your eyes as you watched his bright smile start to turn into a frown. Knowing that you were the cause of his discomfort only made the ache in your chest grow larger, a small sniffle escaping your lips.

"Don't cry; we'll surely meet again, as long as you keep those feelings in your heart. Well, being in the mood for a scare or two also helps. Who knows? Maybe one day you'll be my next victim!"

Jack said, and you felt the sadness at knowing he was leaving lessen slightly. It had been brief, and even somewhat scary but you enjoyed your time with the tall gentleman, and was honestly sad to see him go. For an adult, he really was a nice person; trustworthy and dependable. You were glad to have met him.

"Yeah…"

You mutter, a small smile creeping up at the corners of your mouth despite the pain in your chest. You only stood there and watched as the tall figure began to walk off into the darkness, form hidden by the tall trees and shadows. You could still make out his figure somewhat, a gangly hand extended your way as he did a sort of flourish.

"May you have a Happy Halloween, and all your nights be full of good natured frights!"

And with that, he was gone, leaving you alone with the adults who quickly came to your aid. The older kids were still immobilized, cries of fear and whimpers escaping their mouths every few seconds. Most of the adults seemed to focus on you, seeing as you were the smallest one in the group. Your disheveled appearance certainly didn't help matters, frazzled hair stuck with leaves and branches, your costume and skin covered in patches of dirt. You just do you best to explain what happened to you, leaving out the part about Jack scaring the children, mostly for fear of being bullied by the kids if they found out. While you were being fussed and fretted over, you did notice that some of the kids had regained their composure by now, tearfully trying to explain what happened. Their story didn't match with yours, and of course they left out the part where they purposefully left you behind; saying instead that they lost you in the woods, desperately trying to find you when they were scared by a random trick or treater. Luckily for you, a few of the adults seemed to take your side of the story, though a couple of them did wonder about said 'mystery' trick or treater. Thankfully the incident was quickly resolved, the older kids being lead home by their angry parents, and you by your own. They were quite worried about you, holding you and showering you with epithets of kindness.

And so that Halloween was brought to a close, with none of you the worse for wear; though you had nightmares about the experience for quite some time afterward, often waking up in a cold sweat, screaming. The dreams were vivid, and terrifying as dreams often were, making your heart pound and pulse race as you ran through the dark forest, dodging trees with their snatching branches. Not all of the dreams were nightmares however; sometimes you did see the oddly costumed gentleman again, who was quite nice as he talked to you and told you stories. You admittedly liked those dreams the best, as they were the most easy for you to remember, and you often drew what little you could recall.

Even as you grew older, and the details of that encounter became muddled in your memory, you never really forgot the kind gentleman who had helped you that Halloween night. You had not seen him since that particular Halloween night but you felt that you would see him again, eventually. You weren't too sure why you had this feeling, only that it was an instinct in your gut. You took the lesson he had taught you to heart, along with the passion he had ignited in you to help others-and be the mood for a good spook or two-his words still rang clear in your mind even now, years later. Little did you know that that small encounter would be a prelude to a grand adventure, and the step on a path in which both of your fates would intertwine; for better or for worse.


End file.
